Coupling of steroid O-(carboxymethyl)oxime derivatives with single-protected alpha,omega-diaminoalkanes

Citation
V. Pouzar et al., Coupling of steroid O-(carboxymethyl)oxime derivatives with single-protected alpha,omega-diaminoalkanes, COLL CZECH, 64(12), 1999, pp. 2035-2043
Citations number
13
Categorie Soggetti
Chemistry
Journal title
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS
ISSN journal
00100765 → ACNP
Volume
64
Issue
12
Year of publication
1999
Pages
2035 - 2043
Database
ISI
SICI code
0010-0765(199912)64:12<2035:COSODW>2.0.ZU;2-Q
Abstract
New approach to the synthesis of steroid oximes bearing O-substituents with terminal amino groups was described. The easily accessible steroid O-(carb oxymethyl)oximes were reacted with single-protected Boc-alpha,omega-diamino alkanes to give corresponding amide intermediates. From them the Boc protec ting groups were cleaved with trifluoroacetic acid to afford the desired st eroid derivatives with terminal amino groups. The procedure was succesfully tested on steroids with O-(carboxymethyl)oxime group in positions 7 and 17 . The decomposition of target products was observed during deprotection of substituted 19-oximes.